


(500) Days of Dean

by WuvWinchesterHugs



Series: Crossovers [3]
Category: (500) Days of Summer (2009), Supernatural
Genre: Angst, Break Up, Dean Winchester Does Karaoke, First Kiss, First Meetings, First Time, Flashbacks, Hurt/Comfort, M/M, Past Relationship(s)
Language: English
Status: Completed
Published: 2019-08-13
Updated: 2019-08-13
Packaged: 2020-08-20 20:29:10
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 24
Words: 17,169
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20233894
Author URL: https://archiveofourown.org/users/WuvWinchesterHugs/pseuds/WuvWinchesterHugs
Summary: This is a story of boy meets boy. But you should know, this is not a love story.





	1. Prologue

**Author's Note:**

> This is a story that's being republished as a multi chapter fic, rather than a verse.

Note: The following is a work of fiction. Any resemblance to persons living or dead is entirely coincidental.

Especially you, Stanley Merwin

Asshole.


	2. Us

**Summary for the Chapter:**

> The first boy, Castiel Novak of Pontiac, Illinois, grew up believing that he'd never truly be happy until the day he finally met, “the one”.
> 
> The other boy, Dean Wesson of Lawrence, Kansas, believed the exact opposite.

This is a story of boy meets boy.

_Day 1_

The first boy, Castiel Novak of Pontiac, Illinois, grew up believing that he'd never truly be happy until the day he finally met, “the one”.

As he sits in on a meeting, thinking back to his younger years, he remembers that this belief stems from early exposure to sad music, and and a complete misreading of The Graduate.

The other boy, Dean Winchester of Lawrence, Kansas, believed the exact opposite.

Since the death of his mother, and the eventual pulling away of his father, Dean could honestly say he only loved two things.

The first one was his short, spiky hair.

The second was how easily he could just shave it off when it started to get shaggy, and feel nothing.

Castiel, Cass for short, meets Dean on January 8th, the same day of that meeting.

As he looks down to watch Dean work, Cass knows almost immediately who he's been looking for.

This is a story of boy meets boy, but you'd do well to keep in mind, this is not a love story.


	3. Love Kills

**Summary for the Chapter:**

> “I think we should stop seeing each other.”

_Day 290_

A young boy rides his bike downtown, straight to the apartment building, ties up his bike on the rack, and hits the button to be bussed in.

Once the door buzzes, he barges right in, straight to the door that's slowly opening, greeted by two men at the door.

The longer haired one, Gabriel, greets him, “We didn't know who else could help.”

The other, Balthazar, tells him, “It's Hannah all over again.”

The boy just looks back at them, and says,

“You did the right thing.”, taking off his helmet and asks, “So where is he?”

Before either Gabe or Balthazar can answer, a loud crash can be heard, and they all turn their heads to the source: Castiel, smashing plates one by one, robotically.

But before he can smash another one, Cass hears, “Castiel.”

And that stops him, turning his head towards the newcomer, “Jack. What are you doing here?”

Jack tells him, completely sympathetic, “I came to help.”

Cass thinks it has to be a joke, considering how he feels, “Help me how?”

Jack focuses on the more immediate matter, “Well, first off, put the plate down.”

Cass stares at the plate for a moment, like he completely forgot he'd been about to smash it.

But finally, he sets it down, following Jack towards the couch, and Jack hands him a glass of clear liquid. “Drink this.”

Cass drinks it all in one gulp, as Balthazar asks, “What was that?”

Jack tells him, “Vodka.” as Cass feels obligated to ask,

“Does Dad know you're here? Gotta be past your curfew.”

Jack just sighs and says, “Don't worry about that. Why don't you start from the beginning, and walk us through what happened?”

It's the absolute last thing he wants to do, but Cass also knows he's gonna have to talk about it eventually, so slowly, he begins.

“Things were going very well.”

He thinks back to all those moments that had seemed so perfect. The hand holding, the kisses in bed. The emotional hugs, and that time he got Dean to smile by showing him an album from his favorite artist.

“Then what?” Jack asks, bringing him back to reality.

Cass definitely doesn't want to talk about that, because it's still so fresh, but he still forces himself to say it.

_“I think we should stop seeing each other.” Dean says at the diner._

Jack's surprised, “Just like that? No warning?”

Cass confirms, “No warning.”

Gabe tries to help, “Did he even say why?”

_Dean looks right at him, as he says honestly, “I mean. This thing we're doing. What are we doing? Is it normal?”_

_Cass, unable to process what Dean just said, tries to say something, anything, to salvage this, “Normal? I...I dunno. And I don't care. I'm happy. Aren't you?”_

_Dean's confused, “You're happy?”_

_Cass is equally confused, “You're not?”_

_Dean tries to get Cass to see his side, “All we do is argue.”_

_Cass isn't having it, “That's wrong.”_

In the present, Jack tries to be comforting, “Maybe he wasn't in the best mood.”

Gabriel chimes in again, “Maybe a manly man...guy... type... thing.”

Balthazar asks, “So then what?”

_“You can't seriously say you didn't see this coming. Come on. We've been Sid and Nancy for a while now.”_

_Cass has to remind him, because if Dean seriously thinks he's using that analogy correctly, he's just wrong. Plain and simple._

_“Dean, Sid stabbed Nancy seven times. You can't be serious. We don't always get along, but I'm not Sid Vicious.”_

_But Dean wasn't thinking that at all, “No, see, that's what you aren't getting. I'm Sid.”_

_But Cass doesn't like that analogy either, “So I'm Nancy?”_

_But then their waitress shows up with their order, with Dean's pig-in-a-poke breakfast, and Cass’ soft boiled egg._

_“Let's just eat, then we'll keep talking later.”_

_Cass doesn't even touch his food, but Dean just digs right in, like he didn't just break Cass’ heart._

_“Mmm. Delicious. Really glad we did this here. Love me some pig-in-a-poke.”_

_When Dean looks up, he notices Cass is still staring at him blankly, so he asks, “What?"_

_Cass seriously can't believe Dean's acting like nothing's wrong, after everything just said._

_Seeing absolutely no reason to still be here, Cass gets up and starts walking away._

_But not before he hears Dean say, “Wait, Cass, don't leave. I still think you’re my best friend!”_

Everyone in the present flinches when they hear that part, but only Jack tries to make Cass see reason.

“You've dumped people before.”

Cass can agree with that, “Yes.”

“And people have dumped you before.”

But Cass can't focus on anything, or anyone, else, “But this was different.”

Jack asks, “Why?”

Cass says simply, “Cause it's Dean.”

Balthazar tries to be encouraging, “So what? You'll meet someone entirely new. All I'm trying to say here is, you're one of the best guys I know. You'll get over him.”

Gabe offers his own encouragement, “It's just like they say. Plenty of other fish in the sea.”

Cass immediate shoots that down, “No.”

Gabe plays dumb, “They do say that.”

Cass shoots it down again, “Well, they're liars. I don't want to get over him. I want him back.”

There's an awkward silence when Cass says that, but Cass doesn't care. Dean is the one, and he's gonna get him back.


	4. Message in a Bottle

**Summary for the Chapter:**

> Dean Winchester was a man. Height, above average. Weight, average. Boot size, also above average.
> 
> For all intents and purposes, Dean Winchester was just another tall guy.
> 
> Except he wasn't.

_Day 1_

Cass is in a meeting, kind of zoning out, while Balthazar is talking about ideas for a new holiday.

It should be noted that Cass is a greeting card writer at a popular card company, along with Balthazar.

Cass’ boss turns to him once Balthazar sits back down, asking,

“Whaddya think, Novak? Wanna write up some prototypes for this?”

But then, a man walks up to his boss, telling him about a caller in line three, which prompts the boss to introduce him,

“Everyone, his is Dean. My assistant. Just moved here from…” he turns back to Dean, having forgotten, and Dean supplies, “Kansas.”

“Kansas. Right. Dean, everyone. Everyone, Dean.”

Dean tries to get away from the awkwardness by saying, “Nice to meet you.” and dismissing himself, walking away.

It should be noted here there are only two types of people in this world. Men, and women.

Dean Winchester was a man. Height, above average. Weight, average. Boot size, also above average.

For all intents and purposes, Dean Winchester was just another tall guy.

Except he wasn't.

In 1998, Dean quoted the actor James Dean, for his senior quote in the yearbook,

“Live fast, die young, and leave a good looking corpse.”

This spike in the Kansas sales of his films continues to puzzle industry analysts.

Dean's employment at the movie theater during his sophomore year coincided with an inexplicable 212% increase in revenue.

Every apartment Dean rented was offered at an average rate of 9.2% below market value.

And his commute to work, which involved a long walk to his 1967 Impala, averaged 18.4 double takes a day.

It was quite a rare quality, this “Dean effect.”

Very rare, and yet something many post adolescent men have encountered at least once in their lives.

For Castiel Novak to find it now in a city of countless offices, slightly less commercial buildings, and 3.8 million people, Cass was convinced that it could only be explained by one thing:

Fate.

_Day 3_

Cass is checking Dean out when Balthazar tells him,

“I hear he's a real asshole.”

Cass breaks from his staring long enough to ask, “Really?”

Balthazar confirms, “Yeah. Someone tried to talk to him in the copy room, and he just wasn't having it.”

Cass defends Dean, “Maybe he was in a rush.”

Balthazar says, “Or maybe he's a manly, ‘i’m on top of the world’ superdick.”

Once he stops to consider it, Cass decides Balthazar might be right.

“Damn.”

“I know. He's pretty hot for a guy.”

Cass can't help the bad mood that's creeped into his voice, “It's unsettling. Why's it always gotta be the cute guys that think they can treat people like meat and get away with it?”

Cass shakes his head then, “No, you know what? Forget him. I don't even care. That's how he wants it? Fine.”

_Day 4_

Cass has his headphones on as he walks into the elevator, completely oblivious to his surroundings, when who should walk in right before the doors slide closed but Dean Winchester.

Cass keeps feigning obliviousness, now that he knows Dean's true colors, but Dean points to his head phones, saying something Cass can't make out.

Cass just waves and says, “Hello.”, but when Dean says something again, his curiosity gets the better of him, and he pulls one ear off asking, “What was that?”

Dean says again, “I love the Police.” gesturing to his headphones.

Cass is momentarily paralyzed, so Dean tries again, “You got good taste in music.”

Cass asks him, having broken his paralysis, “You like the Police?”

Dean gives him a small impromptu concert, singing along with Cass music, “Sending out an SOS. Sending out an SOS.”

Once that part stops, Dean tells Cass, “Love em.” before the elevator door opens, and Dean gets off, and Cass is left watching him go.

“Wow.” is all he says, as the elevator door closes.


	5. Bad Kids

**Summary for the Chapter:**

> It's a coworkers engagement party at the office, and it's in full swing. The cake’s being sliced up and passed around, as are drinks, when Cass, on a whim, grabs two glasses and goes looking for a certain green eyed freckled person.

_Day 8_

It's a coworkers engagement party at the office, and it's in full swing. The cake’s being sliced up and passed around, as are drinks, when Cass, on a whim, grabs two glasses and goes looking for a certain green eyed freckled person.

Eventually, he finds Dean by himself, not really talking to anyone, possibly looking a little bored.

“Oh, hello. Dean, right?”

Dean looks up, smiles, and responds, “Yeah, that's me. And you're…” He trails off, then points, “Police fan.”

Cass nods, “Yes. I'm Cass.”, then offers Dean one of his drinks. “You want some…” but trails off, cause his minds drawing a blank, “I don't know what it is, but it's not champagne.”

But Dean just takes it, “Sure. Always love a drink.”

There doesn't seem to be anything else to talk about for the moment, so Cass tries another approach, “So, how are you?”

Dean, unfortunately, is no better at it than Cass is, and just says, “Pretty alright.”

Cass asks him, “Did you just move here?”

Once Dean confirms, Cass then asks, “When was that?”

“Saturday.”

Naturally, Cass is surprised, “That's...wow. What, um, brought you here?”

Dean shrugs, “I dunno. Wanted something new. Something that wasn't where I used to live.”

Cass nods, and attempts at a joke, “Then you're definitely in the right place.”

They both laugh at that for a good few minutes, but then they realize the party's moving back downstairs, and follow the crowd.

Dean asks Cass, “You work here long?”

Cass answers honestly, “Only about 3 or 4 years.”

Dean seems a little surprised by that, “Wow. So, what, you always wanted to write greeting cards?”

Cass laughs at this, and again, answers honestly, “No. I don't think I even want to do it now.”

Dean then says the next logical thing, “Then quit. Do something else.”

Cass agrees, “Probably. Actually, I studied to be an architect.”

Dean impressed by that answer, “Oh yeah? That's pretty cool. So what happened?”

Cass shrugs, “Just didn't work out. Needed a job that would actually have me, so here I am.”

Then, now that they've moved back to Cass’ desk, Dean asks, “You any good, at least?”

Cass picks up a prototype and hands it to Dean, “Well, I did write this one.”

Dean flips open the card and reads it out loud, “You found the peanut butter to your jelly. Congratulations on your engagement.” Dean looks at Cass, “That's pretty good.”

Cass answers, maybe bragging a little, “Actually one of our bestsellers.”

Dean jokes, “No, I meant as an architect.”

Cass tries to laugh back, “Yeah, I highly doubt that.”

Dean tries to make him feel better, “Well, at least you got some talent as a greeting card writer.”

Cass tries for a joke of his own, “Thank you. Actually I had a similar nickname in college. Mr. Talent.”

Dean misses the joke entirely, and responds, “They called me Mr. Anal.”

Cass spits his drink out at that. Whatever he was expecting, it definitely wasn't that.

Dean either doesn't get why Cass overreacted, or he's pretending not to, as he says, “I was a bit controlling whenever I had a group project."

Cass nods in understanding, but it's pretty obvious that whatever moment there could've been between them, has been shattered.

With that, Dean dismisses himself, “I should be getting back to…” and walks back to his desk.

Cass calls faintly, “All right. Talk to you soon.”

Once Dean's back at his desk, inspiration hits Cass like a bolt of lightning. Within seconds, he's pulled out some paper and started sketching a skyline.

But within seconds, he finds himself erasing it, until finally, he just throws it in the trash. Oh well.


	6. Please, Please, Please, Let Me Get What I Want

**Summary for the Chapter:**

> “I'm not so sure about it, but I think it's official. I'm in love with Dean.”

_Day 154_

Cass and Gabriel are walking down the street, when Cass tells Gabe, “I'm not so sure about it, but I think it's official. I'm in love with Dean.”

Gabe doesn't have a chance to respond before Cass continues,

“I love his cocky smile.

I love his spiky hair.

I love his bowlegs

I love all the little freckles on his face.

I love his Blue Steel face.

I love how he throws his head back and laughs.

I love how relaxed he looks when sleep takes him over.

I love how I hear the song Highway to Hell, and every single time, I think of him. I love how he makes me feel. Like, I can do anything. Or, like I want to break the rules.”

Cass just abruptly walks away after that, which prompts Gabriel to say, while shaking his head,

“This is definitely not good.”

_Day 11_

Cass is playing a video game with Jack, while also telling him about Dean

“He likes the Odyssey and Kurt Vonnegut. We talked about Scooby Doo for about 20 minutes. Can't believe how compatible we are. Actually, he's not even close to what I thought at all. He's so incredible.”

Jack just rolls his eyes as he tries to simultaneously focus on the video game, “Oy vey.”

Cass, unable to see what the problem is, asks, “What?”

Jack just points out the obvious, “Just because you and a hot guy happen to get along, _does not mean you're supposed to be together! _”

Cass has no clue what Jack is talking about, “What do you mean?”

_Day 22_

Cass, Gabe and Balthazar are sitting at a bar where Cass tells them,

“It's over.”

Gabe and Balthazar ask together, “What?”

“Me and Dean.”

Balthazar asks, because he has no tact, “Was it really on in the first place?”

Cass rolls his eyes, and tells them, “No. But maybe if we lived in a world where things happen like they're supposed to, something might've been.”

Gabe is no help either, “Yeah, well, sorry, but we're in reality, not someone's sexual fantasy.”

Balthazar finally asks, “So, what exactly happened?”

Cass has been waiting for this, so he starts, “So we're in the elevator. We got nine more floors to ride, and it's just us. I asked how his weekend was, and he says it was good. Can you believe that?”

Naturally, Gabe and Balthazar are completely confused, “I'm sorry. Believe what?” “Did we miss something here?”

“He said, 'it was good’. Emphasis on the good. He might as well have said he spent the weekend boinking some hot long haired yoga instructor. Jerk. But whatever. I'm over it.”

Balthazar has to point out what an idiot Cass is being, “What the hell is wrong with you?”

Cass just lays it all out, “He's not interested in me like that, and there's nothing I can do about that.”

Balthy asks, “Just because he said he had a 'good’ weekend.”

Cass tries to tell him, “And other things.”

Gabe tries to see if he can help, “Did he say hi instead of hey? Cause you know that means he's straight, right?”

But Cass isn't interested in that, “Look, I gave him tons of chances.”

_Dean walks up to Cass desk and asks the people in the area, “Heading to the supply room. Anyone need anything?”_

_Cass sees this as an opportunity, and says, very awkwardly, “Oh, you know what I need?”_

_But Dean just stands there, waiting for an answer, and Cass has to cover, quick,_

_“Toner.”_

_Dean nods, “Sure. No prob.” And walks away._

_Another time, Cass plays a Police song, loud enough for Dean to hear all the way at his desk._

_When Dean shows no sign of hearings it, Cass puts it up a little higher, but all Dean does is clean up his desk and leave._

Back in the present, Cass is now telling them,

“Whatever. It's alright. I don't need these mind games. It's just, you you know. I'm fine where I am. I'm not tangled up in knots.”

He pauses for a minute, before he muses, “Lot of people don't realize it, but being alone, it's actually not so bad.”

Gabe just tells him flat out, “Just ask him out already.”

Cass shakes his head, “Don't be an idiot.”


	7. Here Comes Your Man

**Summary for the Chapter:**

> “It's actually a work thing. The whole office will be there.”
> 
> “Couldn't even if I wanted-.”
> 
> “Did you not hear what I said? The whole. Office. Is. Going.”

_Day 27_

Cass is listening to music at his desk, when Balthazar, whose desk is right next to him, gestures for him to take his headphones off.

When Cass finally does, the first thing Balthazar says, “Tomorrow night. Karaoke.”

Cass has no problem telling how he feels about that plan, “No.”

Balthazar tries to goad him, “Come on!”

“After how wasted you got last time? Not a chance.”

Balthazar waves it off, “I wasn't that bad.”

Oh yeah? Let Cass remind him how bad he was, “You started screaming at everyone, tried to hump one of the other singers, and told everyone they should try to start an orgy.”

Balthazar, of course, only focuses on the positive, “But nobody took me seriously, did they?”

Cass doesn't care, “Still not going.”

Balthazar informs him of the real reason he's bringing it up, “It's actually a work thing. The whole office will be there.”

Cass has gone back to focusing on his computer, dismissing, “Couldn't even if I wanted-.”

But Balthazar isn't about to let Cass ignore him like that,

“Did you not hear what I said? The whole. Office. Is. Going.”

And that, of course, makes Cass look over at Dean, who's currently helping a coworker.

Cass smiles then, because ever since he'd just about given up, this opportunity arose. This could be his shot.

_Day 28_

Balthazar is already singing a horrible rendition of INXS’ 'Need You Tonight’, and Cass makes a beeline straight for Dean, who's closer to the stage, greeting him,

“Hi.”

“Hi. Wait. Everyone said you weren't coming.”

Cass is flattered, “You asked if I was-.”

But he never gets a chance to finish, cause right then, Balthazar finishes, and grabs Cass in a bear hug.

And wouldn't you know it, Dean's name gets called next, so he downs a shot, and says, “That's me. Gotta go.”

Dean goes over to the stage, attempting to adjust the mic to his height,

“Hey. Not new to karaoke, but new to this place. No teasing, alright?”

Of course, Dean's a natural, even with a song like “I'm Too Sexy.” Cass can't stop smiling as he watches the performance.

Afterwards, Cass grabs two drinks, heads to the booth where both Dean and Balthazar are talking, and interrupts the conversation,

“Hello.”

Dean turns, and upon seeing Cass, smiles.

Cass goes on, passing the second drink to Balthazar, telling Dean, “Didn't think you'd wanna join us. Would've gotten you a drink.”

Dean just holds up his bottle, “I'm covered, man.”

Cass just has to compliment his performance, “You were... interesting to listen to.”

Dean nods, “Thank you. Wanted to sing, ‘Cherry Pie’, but guess they didn't have that one.”

Balthazar tells Dean, drunkenly, “Castiel's from Illinois.”

Dean raises his eyebrows, “Really?”

Cass confirms, “I did. Lived there almost my whole life. Until I was in my 20s.”

Dean brings up the song again, “I actually named my dog after that song.”

Cass totally misses it, asking, “What was her name?”

There's an awkward silence, before Dean supplies, “Cherry.”

But, perhaps Dean chose to forgive him, since they're all a little tipsy.

Balthazar gets right down to it, “You dating anybody?”

Dean has no problem answering right away, “No.”

Balthazar asks, “Why?”

Both Cass and Balthazar are surprised at Dean's answer, “No one's looking, and neither am I.”

Balthazar, the drunk bastard, has to be a dick here, “I don't believe you.”

Dean challenges him, “You don't believe a guy can be fine living alone without throwing sex into it?”

Balthazar then asks the next rude thing, “Are you straight?”

Dean dodges it, “None of your business. I just don't really feel the need to attach myself to someone. I actually don't feel the need to attach myself to anything.”

During this whole thing, Cass is just staring at Dean with a dorky smile on his face.

Dean decides to just lay it all out, hopefully ending this conversation for good,

“Alright. I'll just come right out and say it. I'm okay just having fun my way. Relationships complicate things, and people get hurt when things don't go the way they want to. Who needs that crap anyway? We're still young, right? We live in a city where it's okay to want to be young. Why not just sit back and enjoy it, and save the boring stuff for when we're grumpy old men?”

But finally, Cass has to know something about all of that, “But what happens if you find the one?”

Dean laughs at hearing that, prompting Cass to go, “What?”

“You don't actually buy that chick flick crap, do you?”

“It's the one. Not the tooth fairy.”

“What does that even mean? I mean, seriously? It's not like I haven't been in relationships before, but I don't think any of them were it. Not to mention, you've seen today's divorce rates.”

Balthazar pipes up again, not being even remotely helpful,

“Methinks the man doth protesth too much.”

But Dean's ready for it, “No.” Then he turns back to Cass, “There's no such thing as the one. It's made up.”

Cass can't let this go, “It just so happens I think you're wrong.”

Dean clearly is getting uncomfortable with all of this, so he challenges Cass, “Fine. What exactly am I supposed to be looking for?”

But Cass doesn't think Dean really wants instructions, so he goes for a different approach,

"You'll know. Regardless of who it is, or how you meet, somewhere deep down in your soul, you'll just know.”

For a second it looks like Dean might have taken those words to heart, but he just sips his beer and says, “Agree to disagree.”

But then, out of nowhere, Dean nominates Cass, and after stumbling around while singing, somehow, they wind up back at the bar, trying to figure out the tune of a theme song they both love.

Naturally, Balthazar is back to singing, but in the middle, he just stops, and that's when Cass and Dean decide to help Balthazar into a taxi to take him home.”

They make it all the way to the open car door, before Balthazar suddenly turns himself around, and says, “Hey.”

Cass, trying to be a good friend, asks, “Yes?”

But Balthazar points at Cass, “Not you.”, then points at Dean. “You.” He thumbs back at Cass whole still looking at Dean. “He likes you.”

Cass, upon hearing that, shoves him into the car, “Alright, that's enough.”

“Just tell him alre-.” Balthazar is cut off by the door slamming, and the taxi drives off.

Cass is all apologies, “I'm sorry. Don't know what it is about him and karaoke.”

Dean asks, “Is it true?”

Cass misses what Dean was getting at, “Yeah. Completely. Every single time.”

Dean shakes his head, “No, not that. The other thing.”

Cass plays dumb, “What other thing?”

Dean asks gently, “So you...like me?”

Cass tries to play it off with a laugh, “Of course I do.”

Dean tries to test him, “As friends, right?”

Cass doesn't have the heart to correct him, “Of course. As friends.”

But Dean needs to make sure, “Only as friends?”

That leaves Cass stuttering his way through the truth, “Yeah, I don't know. Have thought much about-. Yes. Why?”

Dean tells him, “No biggie. Just think you're a really interesting guy, and I think we should be friends. Can we do that?”

Cass can feel his chances dwindling away, but he agrees, “Yes. You and me, we can be friends.”

Dean smiles, “Good.”

They stare at each other for a few moments, before Dean breaks the moment, “Well, I'm heading this way, so...”

And that's it. Dean walks away, Cass again just stares after him, wondering if he just blew it.

_Day 31_

Cass is in the copy room when Dean comes in. Cass is already working on his stuff, but Dean takes a second or two to set himself up.

Other than an exchange of, “Hi”s, they don't really talk.

Cass has no idea how Dean feels, but for Cass, he can't help but feel awkward. He stares at Dean, whole Dean just stares off somewhere else.

Cass attempts to fix it, turning his head, “So, that night was awkward.”

But he's surprised to find Dean is now standing right next to him. And not only that, but Dean actually leans in and kisses him.

Their work is temporarily forgotten as the kiss happens, but Cass wishes it didn't have to stop.

But all too soon, the kiss is over, and Dean goes straight back to his copy machine and finishes up his work, gives Cass a smile, and leaves.

Huh. Maybe Dean doesn't wanna be just friends after all.


	8. Chapter 8

_Still Day 31_

At Cass’ apartment, there's a continuous banging on the front door, which doesn't let up until Cass finally goes to answer it.

It's Gabriel, and he's pissed, “You son of a bitch.”

Cass opens the door wider to let him through, whole also attempting to shush him.

“Seriously? The same guy you've been oogling over for weeks?”

Cass attempts to defend himself, “It wasn't oogling.”

“The guy you said was completely out of your league, that you never would get a chance with. That guy?”

Cass tries again to get him to calm down, “Gabriel, please.”

Naturally, Gabe gets right down to it, “You boink him?”

Cass immediately objects, “No!”

Gave keeps going, “Hummer? Handy?”

Cass keeps denying, “No, Gabriel. There were no jobs. We just kissed.”

Gabriel doesn't believe him, “Come on. I'm one of your best friends. The one that put up with all your lovelorn laments about this guy for weeks. You were checking all those boxes for stalking!”

Cass tries one more time, “Gabriel, shut up.”

But it no longer matters, because a door can be heard opening, and wouldn't you know it, Dean walks right through.

Upon seeing Gabriel, Dean waves, saying, “Hi.”

Gabe is friendly right back, “Heya.”

Dean walks up to Gabe, introducing himself, “I'm Dean.”

Gabe tries to at least be civil, introducing himself as well, “I'm Gabriel. Call me Gabe.”

Dean shakes his hand, “Hi, Gabe. Nice to meet you.”

But then it's an awkward silence, given what, or rather who, they were just talking about, and now with him right there with them.

Luckily, Gabe's not completely oblivious. “I'm just gonna go then. Pretend I was never here.”

Gabe's almost completely out of the apartment, but he turns back, reminding Cass, “Oh, right! Cass, let me know if any jobs happen, alright?”

Cass just shuts him right up, “Goodbye, Gabriel!”

The door can be heard opening and closing, so Cass now has to cover for what just happened.

He turns to Dean, explaining, “He's just...an old friend.” But then he remembers something else. “If you heard that, uh…”

Dean asks nonchalantly, “Heard what?”

Which is indicator enough for Cass, “Nothing. You ready to go?”

Dean walks past him, “Totally. I'm stalking. Scuse me, starving.”

Busted.


	9. There Goes the Fear

**Summary for the Chapter:**

> Dean and Cass are in a furniture store, and Cass attempts to try something they did a while back, pretending to press the microwaves on display.
> 
> “Um, Dean? Our microwaves aren't working.” When he hears no response, he pretends to check the other ones, and says, “None of our microwaves are working.”
> 
> But Dean just gives Cass a blank look, and walks away, leaving Cass to wonder what could've changed between them so fast.

_Day 282_

Dean and Cass are in a furniture store, and Cass attempts to try something they did a while back, pretending to press the microwaves on display.

“Um, Dean? Our microwaves aren't working.” When he hears no response, he pretends to check the other ones, and says, “None of our microwaves are working.”

But Dean just gives Cass a blank look, and walks away, leaving Cass to wonder what could've changed between them so fast.

_Day 34_

“What are we doing here again?”

Dean tries to remember the name, “Uh, something called trivets.”

As they walk past several displays, Cass asks, “How about a flygel?”

But Dean laughs good-naturedly and says, “Nah, not for me.”

They both chuckle at that, until finally, they reach where several home displays are set up, and Cass, out of nowhere, just plops himself down in one of the couches.

“This couch is very... comfortable in our new home.”

Dean sees what Cass is doing, and plays along, sitting right next to him, “Nice little pad we got here, huh?”

He reaches for the remote, “Oh yeah. Dr. Sexy is on.” He pretends to try and change the channel. “Hm. TV doesn't seem to be working.”

Cass just says, “Oh dear.” But then, “I'm hungry. Want some pizza?”

Dean follows Cass to a kitchen display, and Cass goes to the oven, while Dean sits down at the table.

“Smells delicious.”

Cass opens the oven and pretends to pull it out, telling Dean, “It is delicious. I made it myself.”

Dean smiles, looking down at the plate, “Love me some everything pizza.”

Cass reminds him, “Your favorite.”

Cass goes to turn on the sink, trying the faucets, only to discover something, “Sink's broken.”

Dean gets up here, and assures him, “Well, that's alright. Because.” He leads Cass to another section, “That's why we have two kitchens!”

Cass grabs Dean, “Always thinking ahead.”

But Dean's ever the slippery one, “Race you to the bedroom.” and runs towards one of the display beds.

When Cass finally catches up with him, Dean's already lying on the bed, patting the covers for Cass to join him.

Cass does, and upon noticing something, makes a joke, “Um, Dean, I'm not sure how to tell you this, but…”

Dean's full attention is on him, and Cass turns his head towards the door,

“We have a Chinese family in our bathroom.”

Dean follows Cass’ gaze, and sure enough, a Chinese family is staring at them, and all they can do is chuckle, but luckily, the family decides to leave.

With that, the two both turn until they're both on their sides, looking at each other.

“This was fun.” Dean tells Cass, smiling. “You're a fun guy.”

Cass says, “Thanks.” And leans in for a kiss, which Dean reciprocates.

But apparently Dean has something else in mind, because the mood turns serious, “Look, uh... I really need to tell you that, um...I'm not looking for anything serious. That alright?”

Cass doesn't really get what Dean's trying to say, so he agrees, “Yes.”

But Dean apparently needs Cass to understand, because he tells Cass, “You sure? Some people wig out when I tell them that.”

Again, Cass just agrees, “Well, I'm not some people.”

Dean asks, “You sure?”

Cass, however, thinks he can get around that, so he says, “Just something casual, right? Taking it slow?”

That was apparently the right thing to say, because Dean smiles, and says, “Right. Exactly. No pressure.”

Then Dean gets up, Cass following after him, and perhaps that conversation was something Dean really needed to have, because once they're walking again, Dean grabs Cass’ hand, and they keep walking holding hands the rest of the way out of the store.

Much later, they're fooling around in Cass’ apartment, but before it can get too heavy, Cass stops, asking, “Can you wait for a moment?”

Once Dean nods, Cass heads for the bathroom and turns on the light.

Cass goes to the mirror, trying to calm himself down,

“He's just a guy. Just a guy that wants to keep it casual. Hence why he's in my bed right now. But that's casual. That's what you do in a casual relationship. That's fine. Perfect.”

Once that's done, Cass walks back into the bedroom, only to find Dean under the covers, naked.

Cass is so shocked, he can only say, “Hi.”

“Hi.”

Yep. This is definitely a relationship Cass can get behind. And who knows? Maybe he'll get Dean to change his mind.

With that, Cass gets on the bed, and gives Dean a deep, long kiss, and the both of them settle in for one rough night.


	10. You Make My Dreams

**Summary for the Chapter:**

> What can he say, really? He finally scored the man of his dreams, and he can't help it if that just happens to make him feel good about himself.

_Day 35_

The next morning, Cass leaves his apartment with his head held high, an air of confidence following him as he heads to work.

Everywhere he goes, people seem to be in a good mood, every time he looks at his reflection, he actually finds he likes what he sees.

What can he say, really? He finally scored the man of his dreams, and he can't help it if that just happens to make him feel good about himself.

In no time at all, he's at the elevator that takes him to his office, and for the first time in a long time, he has a smile on his face.

  
  


_Day 303_

Cass is exiting the elevator on his floor, now looking completely disheveled as well as crushed. Honestly, if he could've gotten out of work, he would've.

But, one way or another, life had to move on, and if he's being honest, he doesn't really have a legit excuse to skip out on work.

He sits at his desk, unable to not notice that his boss is talking to his new assistant, the one that replaced Dean after he quit.

Across from him, Balthazar asks, “So did you get your loverboy back yet?”

Cass just says vaguely, “It's a work in progress.”

But Balthazar can see that this breakup is hitting hard, so he offers a different kind of advice,

“Try writing a book.”

Cass has no idea what to say to that, so he asks, “What?”

“It's like the great Henry Miller said. Neat way to get over someone is to turn them into literature.”

Cass only has one thing to say about that, “He had much more sex than me. Probably even more than you.”

But then, he gets an email notification. When he looks, he sees that it's Dean.

Cass exclaims, “This is my chance!” and goes to read the email.

“Good to hear from you, man. Not this week, but maybe next? And can I take this to mean you're ready to be friends?”

And just like that, his entire ray of hope is diminished.

Today's gonna be one long ass day at work.


	11. Sweet Disposition

**Summary for the Chapter:**

> For here is Cass, in Dean's world, a place few had ever been invited into to see with their own eyes. And here is Dean, wanting him here. Him, and no one else.

_Day 45_

Balthazar walks into the copy room, only to catch Dean humming something into his phone. This prompts him to turn back and walk over to Cass, who's listening to Dean's humming on his own phone and snickering.

“That's it. I can't believe it took us so long to figure it out.”

Balthazar approaches behind him, and informs Cass, “Dean's gone loco.”

_Day 87_

Cass and Dean are in a video rental place, arguing about what Dean's just declared as his favorite song.

“Can you please just try to be serious?”

“I am serious!”

“No, you have to be joking.”

“I am absolutely not joking in the slightest.”

“‘Your Time is Gonna Come’?”

“Yes! Your Time is Gonna Come is the best Led Zeppelin song ever recorded.”

“Why don't you say 'La La’ while you're at it.”

“I love John Paul Jones.”

“Nobody loves John Paul Jones.”

Dean fires back, “That's part of his charm.”

But then, Dean spots a curtain with a sign advertising adult films, and leads Cass to follow him behind it.

Dean grabs one that looks interesting, “This is one I haven't seen yet. Good reviews too.”

Later, they're at Cass apartment, watching the film, and they're both very entranced by what they're watching.

But apparently, the whole time, it was giving Dean ideas, “Know something? I think we should try it out. Doesn't look hard.”

Within moments, they're in the kitchen, stripped naked, attempting to recreate the move, but it's failing miserably, with their bodies in awkward positions.

“What're you asking me for?”

“This was your idea!”

But luckily, Dean's a good sport, and just laughs, and tells Cass, “Okay, put your hand on the edge of the sink behind me.”

Cass complies best he can, and Dean counts down, “3, 2, 1.”

Cass pushes, but all that happens is he loses his balance and winds up falling on the floor and taking Dean with him.

_Day 95_

Cass is taking Dean for a tour of the city from an architect's perspective.

“From the streets, it's not so exciting.” Cass says now, as he leads Dean on the sidewalk.

“But I if you look up” Cass points upward, “The Arts building. The designers are actually two of my favorites.”

Eventually, they find themselves on a bench where they can look at several architectural marvels all at once.

“This is actually my favorite spot in the city.” Cass tells Dean.

“It is?” Dean asks, surprised. “Why?”

Cass explains, “That's…actually kinda hard to explain. See that building?” He points to one, and Dean nods. “That's been there longer than either of us have been alive.” He points to another one, “And that right there is rumored to have been the first skyscraper to be put in the city.”

Dean seems fascinated by this information, so he tries to point at one himself, “So what's that one?”

Cass asks, “That one?” to make sure Dean's not trying to pull his leg. Dean nods, so Cass has to inform him, “That's just a parking lot. But there's so much more beautiful stuff here though.” He shakes his head sadly. “Just wish people would really stop to appreciate what we have here.” Cass starts to get fired up again, “If I had it my way…” but trails off, thinking it might sound dumb if he says it out loud.

But Dean encourages him, “If you had your way, what?”

Cass shrugs, “Not sure. I'd find a way to make them appreciate it.”

Dean pushes him to keep going, “How?”

Cass appreciates Dean's encouragement, but he still feels a bit shy, “There's plenty you could do.”

But apparently Dean was prepared to do Cass one better, pulling out a pen and telling Cass, “Show me. Come on. I'm completely clueless about architecture.”

Cass takes the pen, and asks, “You really want me to draw something? But there's no paper.”

Dean just says, “Then use my arm. Was planning on getting a tattoo anyway.”

Cass finally decides, what the hell, so he takes Dean's arm, telling him, “All right. Let me see your arm.”

Very slowly, a skyline starts to take shape on Dean's arm, as Cass slowly draws precise lines, careful not to press into the skin too hard.

“First thing I'd do is integrate the buildings better, so to do that, I'd maximize light capacity.”

He pauses to lift Dean's arm to make sure his drawing is accurate, before deciding the drawing is complete.

_Day 109_

Finally, Cass gets invited to Dean's apartment, and Dean immediately apologizes, “Sorry, it's still a bit messy.”

While Dean takes off his outer shirt and sets his keys down, Cass takes a moment to look around the apartment.

For Castiel Novak, this is the night everything changes. The wall Dean so often hid behind, the wall of emotional distance, of space, of casual, is slowly coming down brick by brick.

For here's Cass, in Dean's world, a place few had ever been invited into to see with their own eyes. And here’s Dean, wanting him here. Him, and no one else.

When they're lying down on Dean's bed, Dean asks Cass, “You ever been in the middle of a twister?”

“No, I haven't. But that, and my teeth falling out.”

Dean sucks in a breath, “Me too!”

“Really?”

“Yeah, totally. It's like I'm an old man already.”

Cass laughs good-naturedly, “What other dreams do you have?”

Dean thinks, “Uh, earthquakes?”

Cass calls his bluff, “Really?”

Dean caves, “No.” and laughs.

A little later, after some exploring of each other's faces with just their hands, Dean actually gets deep for a moment,

“You know something? There's this one dream that keeps creeping up, where I'm just driving. It starts out like I'm just driving on some random highway, with nothing but the horizon in front of me. And the road starts to get really bumpy and tough on my baby's wheels. And then I'm driving so fast, it feels almost like I'm flying right off the road. And it's amazing, like that's exactly where I'm meant to be, what I'm meant to be doing. I'm content. I'm happy. But then I realize... something is missing. Like someone is supposed to be there in the passenger seat, but every time I look, nobody's there. It's just me. By myself. Alone.”

Dean pauses here, perhaps thinking of how to finish the thought, but he just says, “And then I'm awake.”

As Cass listens to Dean's spiel, Cass realizes that these aren't stories you just tell someone for the hell of it. No, stories like these, you had to earn someone's trust first before getting the privilege of hearing them.

Cass can feel Dean's wall coming down, and couldn't help but wonder if anyone else ever got this far.

Which is what made the next six words to come out of Dean's mouth even more life-changing.

“I've never told anyone that before.”


	12. Quelqu'un M'a Dit

**Summary for the Chapter:**

> “It's easy, Cass. Quit being a pussy and just ask him.”

_Day 109_

“So what are you two, exactly?” Gabe asks Cass, when they're all at Cass’ place, getting the details.

Cass answers honestly, “I'm not sure.”

Gabe asks, “Well, are you two a couple?”

Cass shakes his head, “It's not that easy.”

Balthazar pipes up, holding a plate of food while talking, “Actually, it is.”

Cass scoffs, “What, like are we serious? Give me a break. We're two consenting adults. We feel how we feel. Who cares what we are? Labels are stupid.”

Balthazar notes, “You sound really, really stupid.”

Gabriel agrees, “You actually do.”

Cass goes on offense, “Okay, number one,” he points at Balthazar, “When was the last time you ever dated anyone, huh?” then he turns back to Gabe, “And you've been with Kali since what, 1998?”

Gabe corrects him, “‘97, thank you very much.”

But Cass isn't fazed, “Okay, ‘97. But, see, that's my point. You two don't exactly have the final say in what a modern relationship should be.”

_Day 118_

“So what should I do?” Cass asks Jack, at one of his swim meets.

Jack tells him the truth, “Ask him.”

Cass was hoping Jack wouldn't say that, and the answer just makes him sigh.

Jack, exasperated, asks, “What?”

Cass tries to explain, “Why push it? Things are going so well. When you start pushing for a label, that's when things go wrong. It's like dropping the L word on the first date.”

Jack nods in sympathy, “Yeah, I get that. It's what happened between me and my last girlfriend.”

Cass is surprised, and demands, “Who the hell was your last girlfriend?”

Jack just says, “The one I had after my last girlfriend before that.” Clearly, Jack doesn't feel like sharing details.

Cass thinks about pushing, but decides to let it go, “So you're saying-.”

Jack just spells it out, “I'm saying you actually do want to ask him. Anyone can see that. You're just worried if you do, you'll get a different answer than the one you want, which will send you into a reality check of how the past few months have actually been. But if it were me, I'd find out now before you show up at his place unannounced, and he's on bed with Justin Smith from Charming Acres, Arkansas.”

Cass thinks this is a weird thing to say “Who's Justin Smith from Charming Acres, Arkansas?”

Jack teases him, “Just some guy he met on a road trip, with Jesus’ long flowing hair.”

But then, the coach calls for Jack to get in the water, and Cass tries to stall for a moment or two, “Wait, coach, I'm not done yet.”

Jack's had enough, so he just states the obvious, “It's easy, Cass. Quit being a pussy and just ask him.”

  
  


Later, Dean and Cass are in Dean's car, driving towards the movie theater. They're not really talking, just enjoying the quiet.

But Cass can't stop thinking about what they're doing. Or, rather, what ARE they doing?

Cass sighs, cause he realizes he really does need to know where he stands.

Dean notices this, and asks, “You alright?”

Cass tries to play it off as nothing, “Yeah.”

Dean pushes, “You sure?”

Finally, Cass decides to bite the bullet, “Dean, I need to know something. What're we... what're we doing?”

At first, Dean's confused, “I thought we were going to the movies.”

Cass clarifies, “Yes, but I meant... what's going on with the two of us?”

Finally getting what Cass meant, Dean answers truthfully, “I don't know. But who cares? I'm happy. Aren't you?”

Seeing he's not going to get a definite answer, Cass decides to just let it go. “Yes.”

But really, Cass is actually okay with Dean's non answer. He's absolutely sure that if Dean had to, he would tell people they're together. He takes comfort in the thought.

With that, the two share a smile, and they continue the rest of the drive in silence.


	13. You Loved Him, You Were Kissing

**Summary for the Chapter:**

> Cass can't let that slide, he just can't, and before he knows what he's doing, he's walking right up and getting in the guy's face, and throwing a punch.

_Day 259_

Cass and Dean are at a bar, and Cass is trying to educate Dean on when fashion was the best.

“London 1964. Last time people really knew how to dress. Now, it's just crazy sunglasses on the back of your head, or body piercings. Or purses big enough to fit a tiny dog on them. Seriously, who said this was okay?”

But instead of agreeing with him, Dean's actually not really interested in the conversation at all, and just says, “Some people are okay with it.”

Cass tries to focus on Dean again, “I like your sense of style.”

But I Dean surprises him by saying, “I was actually thinking about getting a tattoo on my chest. About yea big.” He makes a round circle with his hands.

Cass thinks the whole idea already sounds ridiculous, “No.”

Dean laughs, but even Cass can tell he was actually kind of serious.

But before he can actually say anything else, some jerk sits right next to Dean, greeting him, “Yo.”

But apparently he doesn't realize Dean's with Cass, cause he keeps talking, “How's it going?”

Dean tries to be polite, “Um, fine.”

But the guy keeps talking, “You live near here?”

Again, Dean tries to be polite, while not really giving out any information, “Yeah. Somewhere in the ballpark.”

Dean's entire body language, as well as his words, should be enough to tell anyone that he's not interested, but the guy's either clueless, or he's choosing to ignore it.

“Never seen you around here before.”

Dean tries to give a small hint, “Well, you're not the sharpest tool in the shed, are you?”

But the guy just laughs, “Good one. You're a funny guy.” Then, the guy gets a little closer, “I wanna buy you a drink.”

Dean politely declines, “No thanks, I'm good.”

Which is when the guy actually takes notice of Cass on Dean's other side, “You're with him?”

Cass copies Dean, trying to be polite, “Hi. I'm Cass.”

But just like that, the guy's back to ignoring him, “I don't care.” He turns his attention back to Dean, “Come on. One drink. Pick your poison.”

Dean declines again, a little more forcefully, “I said no.”

Wouldn't you know it, that's when the guy decides to pick on Cass again, “You can't be serious. This guy?”

Cass tries to defend himself again, “Hey-.” But Dean beats him to it, “You know what? Quit being an asshole. As flattering as your offer is, I'm not interested. So why don't you take your lame pick up lines somewhere else and leave us alone? Thanks a lot.”

But the guy's not one to give up as easily, so he turns to Cass, smirking as he says, “Hey. Free country. That's why we have rights now.”

But when neither of them take the bait, the guy finally starts walking away, but not before getting one last zinger in, “I can't believe this bozo here is your boyfriend.” and laughs, before finally walking away.

But Cass can't let that slide, he just can't, and before he knows what he's doing, he's walking right up and getting in the guy's face, and throwing a punch.

Dean looks utterly shocked, and when Cass comes back to his seat, Dean asks, “What the hell are you doing?”

But Cass never gets a chance to answer, because the guy comes right back and lands a solid punch right back.

They head to Dean's apartment, and Cass is still talking about what just happened,

“It was just this surreal thing. It just happened so fast, but actually, it's like the whole thing was happening in slow motion, like everything was just...I don't know. It didn't feel like you'd expect it to “

But then Dean slams a drawer, which tips Cass off that something isn't right here.

“What's wrong, Dean?”

Dean just stands there for a moment, shaking his head, before answering, “I just seriously can't believe you.”

Cass is sure he heard wrong, “You can't believe ME?”

Dean keeps going, “That was just completely not cool what you did back there.”

Now Cass knows he didn't hear wrong, but now he can't believe Dean's actually upset with him, “Are you angry at me? I just threw a punch in for you. And got one back for you too, I might add.”

That's when Dean finally turns to look at Cass, “Oh, so that was for me? That was supposed to be you defending my honor?”

Cass thinks it should be obvious, “Yes, actually, it was.”

Dean tries to simplify it, “Okay, then next time? Don't. Don't need you to rescue me like I'm some goddamn damsel in distress.”

Then Dean moves to his bed, and tells Cass, “You know what? I'm exhausted. Can we talk about this in the morning?”

Cass doesn't know what to say here, and turns to leave, heading for the door.

But then, he remembers something, and he turns back to where Dean's standing.

“Actually, no. I'm not leaving until you tell me what's going on here.”

Dean just blows him off, “Nothing.” he lets out a sigh, before saying, “We’re just…”

Cass asks, “What? We're what?”

Then it hits Cass like a bolt of lightning what Dean's about to say, the one thing Cass knew was going to happen, but foolishly hoped he was wrong.

“We’re just friends.”

And Cass has had it. He can't let Dean get away with saying that. Not this time.

“No! Don't you dare pull that crap with me! You do not treat your friends like this. Our first kiss in the copy room? Holding hands? Kitchen sex? Come on. Friends, my ass!”

Dean goes to sit down then, and he knows he's being a little unfair, but he also did tell Cass up front what his deal was,

“I like you just fine, Cass. I just don't want a relationship.”

But Cass is past the point where he'd allow that to slide,

“Well, guess what! I'm a part of this too, and that means you're not the only one who gets a say! I do too, and I say we're a couple, and that's that! Goddamnit!” and storms out of the apartment, slamming the door shut.

Naturally, neither of them can sleep after that fight. Once, Cass goes to dial Dean, but changes his mind. Regardless of how it came out, he still meant what he said back there.

Cass was fully expecting to be spending the rest of the night alone, lying awake, but apparently someone else had other ideas.

He hears the doorbell ring, and he gets up to answer it, not sure who it could be.

Imagine Cass' surprise when he answers it, and it's Dean, dripping wet from the pouring rain.

But it's Dean who speaks first, “I shouldn't have acted like that.”

Cass asks, “Like what?”

Dean tells him, “Gotten mad at you. I'm really sorry, man.”

Seeing how Dean really does look like he's upset, Cass sighs, and tells Dean,

“It's alright. We don't have to put a label on it. I understand. But I don't think it's asking too much if I'm just wanting some sort of consistency.”

“I know.”

But Cass keeps going, “I need to know that you're gonna not wake up, or leave here, and suddenly change your mind about me.”

But here's where Dean has to be honest, so he gets up in Cass personal space, and whispers,

“I can't do that. Nobody can.”

With that, Dean kisses Cass, Cass shuts the door, and they wind down for a very intimate night.


	14. Old Flames, The Penis Game, Art, and Suffering

_Day 260_

Dean and Cass are lying in Cass’ bed, talking about past relationships, of all things.

“What about you? Did you ever even have a relationship before?”

Dean rolls his eyes, and answers, “Duh, of course.”

Cass prods gently, “Tell me about them.”

But Dean doesn't wanna do that, “Nuh uh.”

“Why not?”

“Because it's not important.”

“I don't care. I'm interested.”

Seeing Cass is going to be relentless until he caves, he tells Cass, “Fine. You wanna hear about my dirty laundry?"

Cass nods, “Yes. I can handle it.”

“Fine. First, in high school, there was Ash Harvelle.”

Cass rolls his eyes, “Quarterback?”

“Nope. Played in a high school cover band. Also had a real knack for hacking. But he was a very sweet guy.”

Cass chuckles, but otherwise doesn't comment.

“Then, in college, there was Jo.”

Cass is picturing some hippie dude, but that shatters when he hears Dean say,

“She was nice enough, but we both knew it wasn't gonna last. Then there was that one semester I took in Greece. Of course, met a hot Greek god, who wasn't shy when it came to nudity.”

Cass is definitely jealous at this point, but he only asks, “That's all of them?”

Dean nods, “The ones that lasted anyway.”

Cass asks, in attempt to try and crack the code, “So what happened? Why didn't they work out?”

But Dean's just as vague as ever, “Same as always. Life.”

_Day 266_

They're sitting on a hill, and Dean's just proposed a new game for them to play.

“That's the most juvenile thing I've ever heard.”

Dean argues, “No, it's not. I swear. Trust me. I'm absolutely serious. Tell you what, I'll go first.”

Dean scooches back a little, takes a breath, and says, “Penis.”

Then he looks to Cass, giving him a shove to encourage him to go next.

Finally, Cass complies, a little louder, “Penis.”

Then Dean again, also louder, “Penis.”

Cass goes louder as well, hoping Dean will realize it's not appropriate what they're doing, “Penis!”

But Dean still gets louder, “Penis!”

Cass is starting to get self conscious, “There's kids. We should stop.”

Dean calls his bluff, “You know damn well there's no kids.”

Embarrassed, Cass goes louder again, “Penis!”

But Dean keeps it up, “Penis!”

Cass asks, “Are you having fun with this?”

Dean nods, “Yes, I am.”

Cass asks in a fit of jealousy, “You did this with your Greek god a lot, didn't you?”

Dean shakes his head, “Not at all. We hardly left the bed.”

And that makes Cass bolder, “Penis!”, only to get dirty looks from someone walking past them.

But that still doesn't deter Dean, “Penis!”

Cass goes for one more time, “Penis!”

But then Dean goes seriously loud, “PENIIIS!”

And Cass claps a hand over Dean's mouth, “Cut that out. Everyone's staring.”

Surprisingly, Dean goes compliant pretty fast, “I'm done. Seriously, I'm done.”

Cass asks, “You're done?”

Dean nods, and Cass removes his hand. “Promise, I'm done.”

It's quiet for several seconds, but really, it's Cass fault for thinking he'd stop so easily.

“PENIIIIIIIIIIIIIIS!!!!!!!”

With that, Cass tackles him to the ground, and they're laughing their heads off.

_Day 191_

Dean and Cass are at an art museum. All the paintings are weird. They look like close-ups of someone's intestines. Or something.

And then, they see a pile of something they're not quite sure of, maybe blocks, or keys, or something else.

Dean attempts to look on the bright side, “It's saying everything, but saying nothing at all.”

But then, they reach a piece that they can't really excuse. It seriously looks like a swirly turd.

Cass asks, “You wanna get out of here?”

Dean immediately agrees, “Yep.”

And they hightail it out of the art exhibit.

They wind up at the movies, where they have a good time, drinking soda, eating popcorn and licorice, which Dean insisted on.

All in all, a pretty good day.

_Day 314_

Cass is seeing some random french film, and can't help but wonder what it would look like if it was based off of him.

_“He is broken.” a narrator says in French, as Cass takes a balloon and keeps walking, getting no joy from the balloon._

_“More than broken, he's alone. His only friend is grief.”_

_Cass keeps walking, until he realizes a mime had been following him. The mime has a look of longing at the balloon, and Cass decides to be nice and give it to him._

_The mime takes it, and smiles for a moment. But then he's back to playing sad, as he slowly releases the balloon._

_They both look up as the balloon floats away, and when Cass looks at the mime again, the mime proceeds to slap him._

_The scene changes, with Cass facing the camera, half his face cast in shadow, while only one side of Dean's face is seen._

_“In any case, suffering.”_

_Cass says, “Suffering.”_

_The narrator, “Endless suffering.”_

_Dean speaks, “So much suffering.”_

_The narrator, “The kind of suffering that doesn't end.”_

_Dean and Cass, one after the other, “Suffering.” “Suffering.”_

_The narrator returns, “A shitload of suffering is what I'm saying.”_

_The scene changes again, this time Cass is on the beach, in a knight's uniform, playing chess with a Cupid._

_Cass makes what he thinks is a good move, then tells the cherub, in French, “Your move.”_

_But the Cupid makes a surprise move, and checkmates him, and responds, “Better luck next time…bitch.”_

_Cass only buries his hands in his face, and the film ends._

_Fin._

By then, the movies already over, and Cass wakes up from his nap.

Seeing everyone's leaving, he decides he doesn't really have a reason to stick around, so he gets up and leaves as well.


	15. I Love Us

**Summary for the Chapter:**

> Cass is sitting at his desk when his boss’ new assistant comes up to him, “Cass? Mr. Adler wants to see you in his office.”

_Day 321_

Cass is sitting at his desk when his boss’ new assistant comes up to him, “Cass? Mr. Adler wants to see you in his office.”

Cass gets up, walks to Mr. Adler's office, and knock.

Mr. Adler looks up, “Cass. Glad you're here. Have a seat.”

Cass moves to one of the chairs and sits down, letting out a sigh.

Mr. Adler decides to just get right to it, “Did something happen to you recently?”

Cass doesn't particularly feel like talking about his problems with his boss of all people, so he plays dumb, “What do you mean?”

Mr. Adler asks, “Did someone die, is someone in the hospital. Something like that?”

This, Cass can say with confidence, “No, sir. Nothing like that.”

But apparently Mr. Adler is more perceptive than he lets on, “Look, I don't mean to butt into your business, but does it have anything to do with Dean quitting?”

Again, Cass plays dumb, “Who?”

Mr. Adler clarifies, “My former assistant.”

Cass just keeps playing dumb, hoping that'll make this whole thing go faster, “Your-.”

That's when Mr. Adler decides to just rip off the band-aid, “Cass, everyone knows.”

When Cass just looks away, Mr. Adler just moves on, “Nevermind. The real reason I'm asking is because lately, your work performance has been a bit off.”

Either Cass genuinely doesn't know what he's talking about, or he doesn't really care, “Not following.”

Mr. Adler picks up a prototype on his desk, “Okay. You wrote this one last week. 'Roses are red, violets are blue.” He opens the card, “'Screw you, assbutt.’” He closes the card, “Call me crazy, but most shoppers on Valentine's day-.”

But Cass cuts him off, needing to know if his suspicions are right, “Am I fired?”

But it looks like he's wrong, as Mr. Adler says, “No! Not at all. You're one of the good ones we have here.”

Cass relaxes a little then, “Alright. I'm sorry. You're right. Things have been a little difficult.”

Mr. Adler is completely sympathetic, “And that's fine. I understand. But perhaps, for work’s sake, you could try channeling your energies towards... something like this.”

Mr. Adler slides some cards to Cass’ side. Cass takes one look at them, and asks, “Funerals and sympathy?”

Mr. Adler nods, “Misery. Sadness. Loss of faith. I think, for where your head's at right now, it's perfect.”

When Cass doesn't object, Mr. Adler dismisses him, “Alright. Glad we had this talk. Back to work. Chop chop.”

With that, Cass gets up and leaves the office, but as he does, he sees a card on a table he helped come up with. Which makes him think back to that day.

_Day 167_

Cass walks into work, feeling like a spring chicken, when Balthazar catches up to him, “Hey. Don't you still need to crank out 20 cards.”

But Cass isn't worried at all, “Not at all. They're all finished.”

But apparently Balthazar has another reason for stopping him, “Can you help me out then? How many different ways can you say 'Congrats’? Cause I think I've hit every one of them. 'Good job’ 'Well done’ 'Way to go’. They're all there.”

Cass thinks about it, before he responds, “Try, 'Every day you make me proud...but today you get a card.’”

Balthazar is impressed, “That's good. I like that.”

Cass is smug, “I know.”

Over in Religious and holidays, he suggests to them, “Why don't you try, 'Merry’?”.

You'd think they'd never heard the word in their life, the way they thank him for his help.

Then, over in the Valentine's Day section, one of the workers says, “We've been stuck on this thing for an hour. Really, anything you can do to help is appreciated.”

Cass thinks on it, but then, he catches Dean's eye, and right then, the perfect line comes to him, and not only does it work, it's what winds up on that card, on that table, after Cass has been put in Funerals and sympathy.

_Day 321_

'I Love Us.’


	16. Train In Vain (Stand By Me)

**Summary for the Chapter:**

> I hate Dean.

_Day 322_

When Cass gets up in the morning, he starts a new mantra.

“I hate Dean.”

He continues his train of thought all the way to work, from when he leaves his apartment, to when he's on the bus.

“I hate his shit eating smile.

I hate his over gelled hair.

I hate his stupid not straight legs

I hate all the little pockmarks on his face.

I hate his stupid fish lips

I hate how he throws his head back and laughs like a hyena.

”

But he finally loses it when he has his music on, and of all songs, Highway to Hell comes on, and without thinking, he shouts,

“I HATE THIS SONG!”

Unfortunately, because he said this out loud, it was enough to disturb the other people on the bus, and the driver actually pulls over and says,

“Sir, I'm going to have to ask you to please get off the bus.”

_Day 345_

Of all things, Gabe and Kali have decided it's time for Cass to start trying to see new people. The girl, April, seems nice enough.

“I usually don't do blind dates, but you came highly recommended from Gabriel and Kali.”

Cass just says noncommittally, “Mhm.”

April tries again, “They told me you write greeting cards. That's super neat. I've actually always wanted to be a writer. I was an English major, but realistically, it's not like that's gonna go anywhere, right? I went to Brown. How about you?”

Finally, Cass can't take it. It's not fair to her. “April?”

April pauses her monologue to ask, “Hm?”

Cass tries to let her down easy, “Listen, it's really nice to meet you, and you're very... attractive. But I really need to tell you up front that this isn't going anywhere.”

April definitely wasn't expecting that so soon, “Oh.”

They're sitting down in a diner, the same one where Dean dumped him, and Cass is telling April the skinny on what happened.

“I liked this guy. Okay, actually I loved him. And what does he do? He shoves a sword right through my heart, literally.”

April looks shocked to hear that, “Literally?”

Cass can't believe he has to clarify that, “No, not literally. Come on. Jesus. What the hell's wrong with you?”

“The point is,” Cass says now, taking a sip of vodka, “I'm fucked up. I really am. On one hand, I want to forget I ever met him. On the other, I just know, that he's the one person on this entire planet that I'm supposed to be with.”

April just nods along, listening.

Cass keeps talking, “You ever do something like this? Thinking back to all the times you had together with someone, replaying it over and over, looking for the signs it was all about to be over? Way I see it, either he's a demon, sent to Earth to cause pain and misery...or he's just soulless.”

Finally, April speaks up, “Can I ask you something?”

Cass takes a sip, and nods, “Okay.”

“He never cheated on you?”

“No. Not at all.”

“He never took advantage of you in any way?”

Cass hesitates, but truthfully, the answer is the same, “No.”

“And he told you up front that he didn't want a relationship?”

Cass confirms, “Yeah.” But he's not really getting what April's trying to point out.

Meanwhile, April looks at him like the answer should be glaringly obvious.

But apparently it just went right over Cass’ head, cause next he says, “Hey. You know what we should do?”

Next thing they know, Cass is singing karaoke drunkenly, while April is just sitting close to the stage, looking extremely bored, before she decides she's not gonna waste anymore time, and gets up and leaves.

Cass sees this, and just says, “That's just great. Buh-bye. Waste of time. You're nothing like Dean."


	17. Mushaboom

**Summary for the Chapter:**

> After hanging up, Cass continues to make his way to his seat, and he's so focused on it, he actually completely bypasses Dean sitting in an aisle seat.

_Day 402_

Cass is getting on a train to a wedding for his co-worker, the same one who's engagement party he talked to Dean at. As soon as he's actually on the train, he pulls out his phone and calls Balthazar, literally the only reason he's even going to this stupid wedding in the first place.

When Balthazar picks up, first thing he says is, “Hello, darling.”

“Hello, Balthazar. Are you already here?”

“Bloody hell, no. I'm not going.”

“Yes you are.”

“No, I'm not. It'll be nothing but a bunch of elders.”

“But you said you were going. That's literally the only reason I am.”

“That's why I did the smart thing and called her the night before and told her I was sick.”

“I can't believe you. I'm not going to know anyone there.”

“Aw, don't be sad. Maybe you'll sack one of the grandchildren.”

Cass is too pissed off to put up with this conversation, so he says, “I'm hanging up.”

“Bye, darling.”

After hanging up, Cass continues to make his way to his seat, and he's so focused on it, he actually completely bypasses Dean sitting in an aisle seat.

Finally, Cass finds his own seat, and hangs up his tuxedo in the above compartment. Once he's settled, he turns his head to look behind him, and confirms that yes, Dean Winchester is on this train with him. He looks just long enough to catch his eye, then turns back, not wanting Dean to think he still cares.

But apparent Dean wanted something else, because Cass hears footsteps, and then, he's being greeted by Dean,

“Hey, Cass.”

Cass looks up, and says, “Dean. I guess I walked right by you. Um, what are you doing? Did you get invited to Millie's?”

When Dean nods, Cass says, “Me too. Guess I forgot you knew her too.”

Dean nods, “Yeah, we worked together all that time, so. But god, I love her. She's so sweet.”

Cass agrees, “Yes. She is.”

Finally, Dean asks, “How are you?”

Cass half-lies, “I'm...good.”

Dean keeps talking, “I sent you an email, but never heard back, so…”

Cass confirms, “Yes, of course. Sorry. I just, you know, got a little crazy. Holidays, so work was just…”

Dean asks, “Still working for Adler, huh?”

Cass nods, “Yes.”

Dean invites him, “I was just gonna grab a cup of joe, if you wanna, I dunno…” Dean seems to get shy here, so he focuses on the book Cass has in his lap. “The Architecture of Happiness. Looks like an interesting read.”

Cass clears his throat, so Dean takes that to mean Cass is done with the conversation, “Well, I won't keep you any longer.”

But Cass has a change of heart, “No no, not at all. You know what? I'll take some coffee.”

Cass follows Dean to the coffee cart, and the rest of the time on the train goes by in flashes.

The two of them talk at a table, and all the things Cass loves about Dean are still there. The smile, the laugh. In fact, if he didn't know better, he'd say that Dean's actually flirting with him.

Before long, they're at the train station, and not long after that, they're at the wedding, Cass managing to get there before Dean does.

When Cass looks back, he sees Dean dressed in a very handsome tuxedo, giving him a small wave. Cass gives one back, and once Dean catches up, they walk to their seats together.

At one point, while everyone else is filling in, Dean leans over to whisper in Cass’ ear, “Penis.”

But there's a time and place to play that game, and a wedding definitely isn't it. So Cass gives a small snicker, and just says, “No.”

The ceremony passes by quickly, and just like that, Millie is pronounced married to her now husband.

At the reception, everyone has a good time. Dean even gets up to dance with the band, and everyone has a good laugh at that.

But somehow, Cass and Dean wind up sitting at a table, talking about their faults.

“That all you got, Cass?”

“Fine. You snore.”

“What? I do not!”

“I'm afraid you do.”

“Nuh uh. I do not. Well, I take that back. You do too.”

Cass acknowledges this, “I know I do.”

But Dean's got another one for Cass, “And your feet are rank.”

Cass can't believe Dean would bring this up now, “One time!”

Dean shakes his head, “Nope. That one time especially, but it's literally every time. Not to mention, your messy bedhead. It's freaking ridiculous.”

Cass fires back a lame retort, “You're ridiculous. Your favorite Zep is John Paul Jones.”

Dean slams a hand on the table, “Damn right. JPJ is the best.”

Cass says, “John Paul Jones-.” But gets interrupted by a kid that tags Dean, calling, “Goose!”

Cass then has to stop their conversation, because Dean proceeds to stand up, and chase after the kid. Dean doesn't tag him though, so he has to go around the table.

But then, it's time for the bouquet toss. At first, Dean and Cass don't move, cause it's supposed to be for girls, but Millie surprises them by encouraging them to get in on it as well.

Not wanting to be rude, they do as she asks, and get right into it, and on the count of three, Millie tosses her bouquet. Everyone reaches for it, straining their arms and nearly knocking each other over, but amazingly, it's Dean who winds up with the bouquet. Cass can't help but smile when he sees Dean caught it. Maybe it's a sign.

Dean and Cass wind up doing a few shots, and surprisingly, Cass manages to work up the courage to ask Dean, “Would you like to dance with me?”

Also surprisingly, Dean accepts, and just like that, they're just another one of the slow dancing couples at a wedding for a coworker.

Once they're comfortable, Dean speaks up,

“Actually, I was wondering if um...I'm having a get together on Friday. Our roof top has a sweet garden. Wanna come?”

If this wasn't a sign of the universe answering him, the universe could go to hell. Here's Dean, with him, slow dancing, looking at him just like he used to, and inviting him to a party that he's throwing.

Cass smiles, and accepts, “Yes. I'd love to.”

Much later, when Cass is back on the train, this time with Dean falling asleep on his shoulder, his smile is the biggest it's been since before Dean dumped him.

_Day 408_

That Friday, Cass walks to Dean's apartment, intoxicated by the promise of the evening. He truly believes, that this time, his expectations will be perfectly aligned with reality.


	18. Hero (Expectation)

**Summary for the Chapter:**

> Dean's get together, expectations vs reality

_Day 408_

Cass gets to the apartment building, and makes way up the stairs. It takes a while, but he eventually makes it there, gift in hand.

Cass knocks on the door, and Dean answers. As a greeting, Dean gives him a peck on the lips, and moves to let him in.

Cass takes a quick survey of the place, and notices there actually aren't that many people here at all. Maybe about 4 or 5 other people, but otherwise, it's just them.

Cass turns back to Dean, and gives him the gift. Slowly, Dean opens it, and once he and once he sees the book Cass was reading, “The Architecture of Happiness”, he smiles, and gives Cass a hug. “Thanks, man.”

They move out to the patio, where they talk some more, and it's like there wasn't a breakup at all. Everything they talked about just flowed naturally, and Cass felt like he was in heaven.

At one point, they move to the edge of the balcony, and keep talking, but suddenly, Dean grabs Cass' hand, and leads him back inside.

Cass has Dean up against a wall, and before either of them are truly aware of it, they're kissing.

They keep kissing and kissing until their lips are swollen, and the rest of the night just passes by in a blur, and when they wake up next to each other in the morning, they share a passionate smile, and Cass knows now more than ever, that they will be together forever.

He makes a mental note to call a local jeweler in the morning, and find the perfect ring.


	19. Hero (Reality)

_Day 408_

Cass gets to the apartment building, and makes his way up the stairs. It takes a while, but he eventually makes it there, gift in hand.

Cass knocks on the door, and Dean answers. As a greeting, Dean gives him a small hug, then moves to let him in.

Cass takes a quick survey of the place, and notices there's actually a bunch of people here. Many of which Cass swears he's never met before. This was definitely not the small get together he was picturing.

Cass turns back to Dean, and gives him the gift. Slowly, Dean opens it, and once he sees the book Cass was reading, “The Architecture of Happiness”, he smiles, and gives Cass a small pat on the shoulder. “Thanks, man.”

They move out to the patio, where one of the many strangers strikes up a conversation with Cass,

“So, Castiel, what is it that you do?”

Cass tells her politely, “I write greeting cards.”

Dean interrupts here to tell her, “Cass here could be one hell of an architect if he wanted to.”

But the same woman keeps talking to Cass, “That's really unusual. How does one go from architecture to writing greeting cards?”

Cass tries to make a joke here, “Guess I just thought, ‘Why make something disposable like a building when I could make something that lasts forever, like a greeting card?’.”

Thankfully, the other guests laugh with him, and Dean gives Cass a cute smile.

Once that conversation ends, Cass somehow winds up near the edge of the patio by himself, sipping his beer and looking at the view.

But mostly, he's watching Dean mingle with all his friends, seeing how good he looks.

The whole thing just makes him go over to where the drinks are and squeeze some lime into his newly poured gin and tonic.

But then, Cass sees Dean showing something off to someone, and it's like time literally stops. He can't move, can't think, he's not even sure he remembers how to breathe. But one thing is for sure, he will not be hooking up with Dean tonight, or any other night ever again.

Finally, when his brain manages to come back online, he moves straight for back inside, back through the front door, all the way out of the building and back to his own apartment.

Cass can feel everything else slipping away, like someone took a giant eraser and just rubbed it all away, until there's absolutely nothing left, except for the faint glint of the ring on Dean's left hand.


	20. The Infinite Pet

**Summary for the Chapter:**

> The place is a complete and utter mess by this point, and when his alarm goes off, it's like he doesn't even hear it anymore.
> 
> But somehow, he actually pulls himself together enough to actually get showered, dressed, and head to work.

_Day 440_

Cass’ alarm clock goes off at 7 sharp, and he smacks a hand down on it to shut it off. But that's about the extent of what he feels like doing today.

_Day 441_

Cass’ alarm clock goes off again, and again, he hits it to turn it off. Since the day before, his nightstand is littered with junk food wrappers.

But today is gonna be different. He gets up to get dressed, and heads right out the door.

And heads straight to the nearest convenience store to buy orange juice, hard whiskey, and all the snack cakes his hands are capable of touching.

When he brings all that to the counter, the clerk gives him a weird look, but thankfully, he doesn't ask questions, just rings it all up and puts it in a bag for him.

As Cass exits the store, a couple holding hands walk past him, and he's still feeling shitty enough to where he just has to say something,

“Hey. You're out in public. Put that away.”

The couple give him a dirty look, but Cass is already moving on, heading back to his apartment in his bathrobe.

_Day 442_

The place is a complete and utter mess by this point, and when his alarm goes off, it's like he doesn't even hear it anymore.

But somehow, he actually pulls himself together enough to actually get showered, dressed, and head to work.

Balthazar is in the phone, trying to get Cass on the phone when he finally sees Cass walk in, wearing a pair of sunglasses.

When Cass sits down at his desk, Balthazar hangs up the phone and tells him, “I've been calling every 5 minutes. You alright?”

Cass so doesn't feel like reliving the nightmare again, so he just says, “I'm alright.”

But Balthazar is too smart for that, “What happened?”

Cass says bluntly, “I don't feel like talking about it.”

Balthazar retorts, “You always feel like talking about it.”

Cass shakes his head, “Not this time.”

Balthazar moves on, “Fine, then. Come on. We gotta go.”

Cass’ bender has thrown his entire calendar out of whack, so he has to ask, “Go where?”

Balthazar moves past him, reminding Cass, “It's Thursday!”

The meeting starts with a coworker showing off new designs featuring a cat.

She gestures to the one on the right, where the cat is on top of a roof and reaching for a bird in the sky, “This one says, ‘Go for it.’”

Then she gestures to the one on the left, where the cat is sitting on a bar stool, one paw on the counter, with a glass of milk next to him, “This one says, 'You can do it.’ It's a whole line of inspirational photographic cards featuring my cat, Deanna. I think they will appeal to our customers. Thank you.”

She goes to sit down, and Mr. Adler praises her, “Good job, Rhonda. Very good stuff. So who's next?”

Mr. Adler turns to Cass, “Anything in Sympathy? Haven't heard anything in a while. Anything to contribute, Novak?”

But Cass hasn't really been paying the slightest attention the whole time, let alone ideas for cards, so he admits, “No, I really, really don't.”

Mr. Adler goes to move onto the next section, but Cass interrupts, “Actually can I say something? About the cat?”

Mr. Adler hesitates, before allowing, “Okay.”

Cass turns to Rhonda first, “No offense, Rhonda, honestly, but this is complete and utter bullshit.”

Balthazar tries to stop him, “Cass…”

But Cass isn't about to be stopped now that he's already started, “'Go for it’ and 'You can do it'? That not inspirational at all. It's suicidal, if anything.” Cass gestures to the card samples, “If Deanna goes for that bird, you got a dead cat on your hands right there.”

Then, he turns back to everyone else, “It's a bunch of lies, and we're the lying liars who tell them.”

Seeing he's got everyone's attention, he keeps going, “Think about it. Why do people buy cards? Cause it sure isn't because they want to say how they feel. It's cause they can't, or they're scared to say how they feel. And here we are, with a service that lets them off scot free.”

Cass stands up here, “You know what? To hell with all of it. Why don't we level with our customers, huh? Let them speak for themselves. I mean-look! What does this say?”

He reaches for a smaller prototype on the table, “Congratulations on your new baby, right? How about instead, we say, 'Congratulations on your new baby. Guess that's the end of is hanging out. Nice knowing you.”

Mr. Adler attempts to regain control of the situation, “Sit down, Novak.”

But Cass is still going strong, grabbing another prototype, “How about this one, with all the hearts on it. Betcha I know exactly where this is going.” He opens it, “Yep! Happy Valentine's day. I love you.” He closes it. “Ain't that something? Ain't it the thing of miracles? This is exactly what I've been talking about. What does love even mean, huh? Does anyone here know? Huh?”

Again, Balthazar tries to get Cass to calm down, “Cass…”

But Cass is beyond help now, “Mr. Adler, if I got this card, I would cover it in holy oil and set it on fire.”, then he throws the prototype back on the desk. “It's just all of it. The damn cards, the movies, the endless number of stupid songs, they're really the ones to blame for all the lies we've been spouting. For all the pain that comes because they didn't prepare us for it. And we're responsible too. I'm responsible. We do a terribly horrible thing here. People should just say how they feel, not just some words somebody else wrote on a stupid card. Words like 'love’ that really don't mean anything at all.”

But then, it's like Cass suddenly realizes what he needs to do. What the right thing to do is here. He grabs his trenchcoat, and says to the entire room,

“I'm sorry. I really am.”

He pushes his chair back in, and says for the record,

“I quit. I'm just done. There's plenty of crap to go around without me adding to it.”

With that, he walks right out, not yet knowing if he just made a huge mistake, or one of the best decisions of his life.


	21. Bookends

**Summary for the Chapter:**

> “I know you truly believe that Dean was the one…” Jack pauses here, worried about how Cass is gonna take the next part. “...but I don't. I really think you're just choosing to remember the good stuff. Do me a favor. Next time you look back trying to figure out what went wrong, promise me you'll give a second look?”

_Day 450_

Cass is at another one of Jack's swim meets, sketching. Once Jack gets the opportunity, he comes out of the water to go talk to Cass,

“Wow. You're sketching again.”

Cass chooses not to make a big deal out of it, since all he's really sketching is a picture of Dean holding a knife. “Just doodling.”

Jack moves to sit on the bleachers, and tells Cass, “20 seconds. Are you okay? Go.”

Cass doesn't want Jack to worry more than necessary, “Yeah. I'm good. I'm alright.”

Jack looks like he buys it for a moment, but then he sees Cass drawing, so he now knows better, and attempts to cheer Cass up,

“Lot of my friends on the team have a crush on you. Like we said. Plenty of fish, right?”

Cass gets Jack's just trying to help him feel better, but he has to remind Jack, “Jack, I appreciate it, but don't forget. There's bigger plans for those fish.”

Jack laughs, so Cass knows Jack wasn't that serious. But it looks like Jack's about to lay some truths on him, starting with, “Hey, Cass?”

Cass is sure he's not gonna like what he hears, bit he's not a complete asshole, so he asks, “Hmm?”

Jack just goes for it, “I know you truly believe that Dean was the one…” Jack pauses here, worried about how Cass is gonna take the next part. “...but I don't. I really think you're just choosing to remember the good stuff. Do me a favor. Next time you look back trying to figure out what went wrong, promise me you'll give a second look?”

The rest is up to Cass, so Jack just pats him on the shoulder and jumps back in the water.

Now that Jack's said it, and he still has no concrete answers, he decides to do as Jack says.

_Dean and Cass are walking down the street. Dean's quickly leaving the copy room after that first kiss. They're holding hands in the furniture store. They're laughing in Dean's car. Then Cass is getting punched in the face by that bar jerk. Cass is yelling at Dean for calling them friends. Dean's showing up to his apartment soaking wet. They're snuggling in bed._

_But then, rather suddenly, the memories stop on a day that Cass has gone over so many times, but instead of going straight to the good parts, it starts towards their get together. Dean and Cass are deciding what movie they wanna see._

_Cass sees a movie that appeals to him, “This one's playing at 5.”_

_Dean asks, “You wanna go see it?”_

_Cass acts nonchalantly, “I dunno. If you want, we could just go back to your place, or…”_

_But apparently Dean was more interested in the movie than he let on, “No, you know what? I just decided. I wanna see it. Let's get going.”_

_The movie turns out to be pretty good, but at one point towards the end, Cass notices that Dean's actually been crying._

_When everyone files out, Cass pulls Dean aside and asks, “Dean? Are you alright?”_

_Dean quickly just brushes it off, wiping the tears away, “Yeah. Fine.”_

_Cass keeps asking, “What's wrong? Was it the movie?”_

_Dean keeps blowing off the questions, “It's nothing. I'm just being a pussy.”_

_Then Dean starts to walk off, Cass following him, and eventually, they're back at the video rental place, talking about music._

_Cass says, “Can't believe we live in a world where nobody's heard of Klaxons.”_

_Dean doesn't appear to be really invested in the conversation, other than to say, “Never heard of them.”_

_Cass appears a little hurt, and reminds Dean, “They’re on that mix I made you. Track 1.”_

_Dean thinks about it, and says, “Right, right.”_

_But then the conversation is forgotten when Cass spots John Paul Jones’ The Thunderthief, pulls it out, and shows it to Dean._

_Dean smiles, and then they make their way out of the store. Cass attempts to reach for Dean's hand, but Dean pulls away before he can._

_Once they're outside, they stand there for a moment before Cass asks,_

_“So, what do you wanna do now?”_

_But Dean instead says, “Actually, I think I'm pretty beat. Gonna call it a day, go home.”_

_Cass is surprised, “You don't want to go get food? You're not hungry?”_

_Dean looks like he's about to say something here, and Cass notices, so he asks, “Are you sure you're alright?”_

_Dean nods, “I'm tired.”_

_Cass agrees, “Alright.” But then, Dean leans in, but instead of going for the lips, he just gives a peck on the cheek._

_For a moment, Cass doesn't move or say anything, but then he says, “I have it. Breakfast.”_


	22. Vagabond

**Summary for the Chapter:**

> The next ten days happen one after the other. Starting with the first one, where Cass is just lying down on his bed, bouncing a tennis ball repeatedly, with no joy in it.
> 
> At least, it starts that way. But then, he starts bouncing it faster, and faster, until he's got it into a rhythm, and that leads to him suddenly being struck with inspiration.

_Days 456 - 476_

The next ten days happen one after the other. Starting with the first one, where Cass is just lying down on his bed, bouncing a tennis ball repeatedly, with no joy in it.

At least, it starts that way. But then, he starts bouncing it faster, and faster, until he's got it into a rhythm, and that leads to him suddenly being struck with inspiration.

First, Cass tears off all the papers on his big chalkboard wall, and erases all the stuff written on it.

Then, he goes to his usual hangout, with his music and several architecture books, carefully paying attention to everything he reads.

Cass gets himself a good suit, and walks into an architectural firm with his head held high, ready for his interview.

When he gets home, he gets the rejection call, and crosses off the firm's name written on the blackboard wall.

Over time, several other firms written on the wall also get crossed off, and when there's almost no names left, he actually throws his chalk, discouraged.

But Cass doesn't throw in the towel. No, instead, he moves to the completely blank section, chalk in hand, and before he knows what's hit him, he's measuring, drawing, shading, and sketching the buildings that have begun to spring to life in his mind.

Inspiration from these buildings come from the view from the rooftop of his apartment building, right outside his window, and his favorite spot in the entire city, in both the day and night.

In fact, by the time Cass actually stops to survey his work, he's practically designed a brand new city all by himself.

Miles away, Cass is blissfully unaware of the fact that at the exact same moment, Dean is getting dressed for the most important day of his life, pulling on his tuxedo jacket.

Simultaneously, while Cass rides the bus to another interview, Dean is at the front of the aisle, with the biggest smile on his face as he stares at the man he'll soon be calling his husband.

But the weird thing is, Cass noticed that while he was so busy trying to get another job, Dean had faded to the back of his mind.

It's funny. Not too long ago, he'd thought he'd never recover from losing Dean, but now, it not only appears he can, he thinks eventually he will.


	23. The Art of Letting Go

**Summary for the Chapter:**

> “Hey, stranger.”
> 
> It didn't matter that Cass hadn't thought about him for several days, he knows now he won't ever be able to truly forget Dean Winchester.

_Day 488_

Cass decides today's a good day to sit at his favorite bench. Sometimes it helps him clear his head.

“Hey, stranger.”

It didn't matter that Cass hadn't thought about him for several days, he knows now he won't ever be able to truly forget Dean Winchester.

Sure enough, when Cass turns to look, there he is, sitting on a bench not too far away from his own. Dean still looks as attractive as ever, wearing a leather jacket and some rugged work pants. Not to the mention, the very noticeable wedding ring declaring Dean off limits.

Dean gets up and moves closer to Cass, telling him, “Thought I might be able to catch you here.”, smiling.

Cass still says nothing, so Dean keeps talking, “You know, ever since you brought me here, I've actually taken the time to come to this place, just to stop and try to appreciate the view like you do.”

Cass finally finds his voice, “So, um, I guess a congratulations are in order?”

Dean teases, “Only if you really mean it.”

Cass half-teases back, “Well, in that case…”

But it looks like Dean's after more than just simple small talk, because Dean moves to Cass bench, asking, “So, are you alright, man?”

As Dean goes to sit right next to Cass, Cass responds, “Eventually, I will be.”

Once Dean's plopped down next to Cass, Dean notices what Cass is wearing, and points it out, “Nice threads, man. Makes you look pretty sharp.”

Cass smiles, “Thanks. I uh, actually quit the office.”

Dean seems surprised, “Really? That's great!”

But then, Cass points out the more upsetting news, “And you seem to be... married.”

Dean nods, his smile now slightly forced, “I know. Crazy, huh?”

Neither of them say anything for a moment, then Cass has to remind Dean, “You know, you really should've told me when-.”

But Dean apparently knows what Cass is referring to, and cuts him off, “I know, man.”

But Cass needs to finish, “When we were at the wedding, dancing.”

Dean attempts to defend himself, because it's technically true, “Well, he hadn't asked me yet.”

But Cass doesn't care, “But he was in your life. So why'd you dance with me, then?”

Dean apparently doesn't seem to get why that's important, so he says, “Cass, I wanted to.”

Cass is just too hurt to really say anything else but, “You just dance to the beat of your own drum, don't you?”

That stung, cause Dean's smile slips a little bit more. But Cass isn't done yet.

“You never wanted to attach yourself to anyone, including me, and now you're someone's husband.”

Dean admits, “Trust me, it surprised me just as much as you.”

But Cass doesn't think that's even remotely fair, “Which is exactly why I don't understand. I've thought about it so much, and I've come up empty.”

Dean only answers, “It just happened, Cass.”

Cass argues, “That's what I don't get. What happened?”

Finally, Dean comes clean, “I just...one day, I looked over at him in the passenger seat of my Baby, and I knew.”

Cass pushes, “But knew what, exactly?”

Dean bites the bullet and just tells him, “What I could never really say to you. I could go without seeing him for a week, and nothing changed. If anything, I loved him even more.”

And that's when it really seems to sink in for Cass that there's really nothing left for him with Dean. And that knowledge hurts.

“You know what hurts more than anything?” Cass says now, because he can't help it.

“Knowing that all the beliefs you've held dear, mean nothing.”

Dean doesn't seem to get what Cass means, “What are you talking about?”

Cass reminds him, “You know. Destiny, fate, 'the one’, true love. All those stupid fairytales. You were right from the get-go, Dean. I should've taken your advice.”

When Cass looks at Dean again, Dean is actually smiling, and Cass has to ask, “What? Why are you looking at me like that?”

Then, Dean tells him something Cass definitely wasn't expecting, “Oh, I dunno. Something to do with the fact that I was sitting in a coffee shop, reading a mechanic magazine, and a guy comes up to me and compliments my baby, which was parked right outside, by my table, and now he's my husband.”

Cass still doesn't get why Dean's telling him this, “Okay. So?”

Dean clarifies, “So, what if I decided to take a road trip? Or gone to a bar instead of the coffee shop? What if I'd decided to leave my Baby at home? It was...it was just meant to be. And you know what? The whole time, that one nagging thought kept creeping up, ‘Cass was right.’”

Cass can't believe it, “Nuh uh.”

Dean backs himself up, “Yes, I did. Looks like the only thing you weren't right about...was me.” Dean says that last part quietly, like he knows it's gonna hurt, regardless.

Dean reaches to hold Cass’ hand for a moment, his ring ever present, but then he pulls it back, saying, “I should probably go. But I'm really glad you're doing so well for yourself.”, then gets up and starts to go.

But as Cass thinks about it, he decides that it's time he finally let all the hurt go. He's been holding onto it for long enough, and he has as many answers as he's gonna get. So, with that in mind, he calls out, “Dean!”

When Dean turns, Cass tells him, “For what it's worth, I really do hope that you're happy.”

And just like that, Dean's smile is back, and then he goes again, officially walking out of Cass’ life.

Now that Dean's no longer here, Cass stops to do what he set out to do here, and enjoy the view. He can feel the weather start to change, and hopes this is a sign of new beginnings yet to come.


	24. She's Got You High

**Summary for the Chapter:**

> Most days of the year are unremarkable. They begin and end with no lasting memories made in between. Most days have no real impact on the course of a life.

_Day 500_

Most days of the year are unremarkable. They begin and end with no lasting memories made in between. Most days have no real impact on the course of a life.

May 23rd was a Wednesday. And on that Wednesday, after Cass had entered the next architectural firm on his list, taking a moment to survey his surroundings, and rode the elevator up to where the interview was scheduled, he sits down on a couch in the waiting room, where only one woman occupies the other couch.

Once Cass sits down, he goes back to looking at all the amazing architecture that went into the buildings interior itself. But he's interrupted when he hears someone ask,

“Are you interviewing?”

Once Cass breaks his concentration, he turns to the other woman, asking, “What?”

The woman smiles and asks again, “Are you interviewing for the position?”

Now that she has Cass' attention, he can answer, “Oh. Yes. Why? Are you?”

She nods, “Yeah.”

Cass nods knowingly, “So I guess you're my competition then?”

Luckily, she seems to feel just as awkward as he does, “Looks that way.”

Cass replies, “Awkward.”

The woman acknowledges that, “Yeah. Definitely.”

Cass attempts to joke here, “Well, then, I hope you don't get the job.”

Thankfully, the woman doesn't appear offended, and actually repeats the same thing back to him, “The feeling’s mutual.”

Then they just look at each other for a moment, and laugh at how ridiculous they both sound.

Once they've done that, the woman asks, “Have I seen your face around before?”

Cass is surprised by that question, “Who? Me? I don't think so.”

But the woman's determined, “Do you ever go to Country Club Plaza?”

Well, that was really interesting, “Actually, I do. It's just about my favorite spot in the city.”

The woman agrees, “Yeah. Okay. Except for the traffic, but-”

Cass tells the, “Yes. Absolutely. I agree.”

But then she tells him, “I think I might've seen you there once or twice.”

Cass definitely didn't expect that, “Really? Weird. Haven't seen you.”

The woman nods, “Maybe you weren't looking.”

Now, if Cass had learned anything, it's that you can't just put great cosmic significance to something as simple as one chance meeting. All anything in life ever is is a coincidence. Nothing more.

Then, Cass gets called back for the interview, and he gets up to follow the man that had called him.

Cass had finally learned that miracles aren't real. Nor was fate, nor was anything really meant to be. He knows that now, he could even say he was absolutely sure of that. Cass was-

“Sorry. Um, I just left, uh, can I head back for a moment?” Cass says to the man he'd been following, and goes back to where the woman is still sitting.

Cass pretty sure.

Once the woman is back in view, he gets her attention, “Hey.”

The woman smiles, and says, “Hello again.”

Cass nods, “I was just wondering if maybe once we're both done here, if you…” he pauses, taking in that big smile on her face. “Wanted to get a drink or coffee or something.”

Her smile slips slightly, apologizing, “I'm sorry. I'm actually supposed to be meeting someone after this.”

Cass is disappointed, but at least he put himself out there. He says, “Okay.” and turns to go again.

But apparently he wasn't giving her enough credit, because the next thing he hears is, “Sure!”

To make sure he heard a confirmation, Cass rushes back to her, and asks, “What was that?”

The woman laughs at his eagerness, and says, “Why not?”

Glad that he asked, he tells her, “Alright. I'll just, uh, wait for you-.”

She helps him out, “Well play it by ear.”

Cass repeats this, “We'll play it by ear.” then he holds out a hand, “My name is Castiel.”

The woman holds out her own hand, “Nice to meet you. My name's Meg. Meg Masters.”

_Day 1_

**Author's Note:**

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